(R)-2-amino-2,3-dimethylbutanoic acid

Base Information

• Chemical Name: (R)-2-amino-2,3-dimethylbutanoic acid
• CAS No.: 53940-82-2
• Molecular Formula: C6H13 N O2
• Molecular Weight: 131.175
• Hs Code.: 2922499990
• DSSTox Substance ID: DTXSID20426344
• Nikkaji Number: J656.282E
• Mol file: 53940-82-2.mol

Synonyms:53940-82-2;(R)-2-amino-2,3-dimethylbutanoic acid;H-ALPHA-ME-D-VAL-OH;(2R)-2-AMINO-2,3-DIMETHYLBUTANOIC ACID;3-Methyl-D-isovaline;L-Isovaline, 3-methyl-;2-METHYL-D-VALINE;ALPHA-METHYL-D-VALINE;?-Methyl-D-valine;H--Me-D-Val-OH;SCHEMBL164980;DTXSID20426344;MFCD01318765;AKOS006341297;AB08748;AC-4452;CS-W011102;DS-8259;HY-W010386;(R)-a-Methylvaline, 3-Methyl-D-isovaline;(R)-2-AMINO-2,3-DIMETHYLBUTANOICACID;F15062;EN300-1268274;A870608;(R)-(+)-alpha-Methylvaline, 99%, >=98.5% (TLC);D-alpha-methylvaline;(R)-(+)-alpha-Methylvaline;(2R)-2-amino-2,3-dimethylbutanoic acid

Chemical Property of (R)-2-amino-2,3-dimethylbutanoic acid

Chemical Property:

• Vapor Pressure: 0.0499mmHg at 25°C
• Melting Point: 144-148.5 °C
• Boiling Point: 217.7oC at 760 mmHg
• PKA: 2.40±0.14(Predicted)
• Flash Point: 85.5oC
• PSA: 63.32000
• Density: 1.038g/cm3
• LogP: 1.14470
• Storage Temp.: Store at RT.
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 131.094628657
• Heavy Atom Count: 9
• Complexity: 122

Purity/Quality:

98%Min ^*data from raw suppliers

α-Methyl-D-valine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C)(C(=O)O)N
• Isomeric SMILES: CC(C)[C@](C)(C(=O)O)N
• Uses: Used in the preparation of medicinal and herbicidal agents. Used in the preparation of medicinal and herbicidal agents

Technology Process of (R)-2-amino-2,3-dimethylbutanoic acid

There total 21 articles about (R)-2-amino-2,3-dimethylbutanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(S)-3-(1-naphthoyl)-4-isopropyl-2,2-dimethyloxazolidin-5-one (1007599-18-9) → (S)-α-Methylvaline (4378-19-2,26287-62-7,53940-82-2,53940-83-3)

Guidance literature:

With hydrogen bromide; In 1,4-dioxane; for 3h; Heating;

DOI:10.1021/ja801165z

Reference yield: 100.0%

(S)-4-isopropyl-4-methyl-2,2-dimethyl-3-(1-naphthoyl)oxazolidin-5-one (1025364-74-2) → (S)-α-Methylvaline (4378-19-2,26287-62-7,53940-82-2,53940-83-3)

Guidance literature:

(S)-4-isopropyl-4-methyl-2,2-dimethyl-3-(1-naphthoyl)oxazolidin-5-one; With hydrogen bromide; In water; Reflux; Inert atmosphere;

With Dowex-H⁺; Inert atmosphere;

DOI:10.1021/ja9039604

Reference yield: 91.0%

methyl (R)-N-benzoyl-2-methylvalinate → (R)-2-amino-2,3-dimethylbutanoic acid (53940-82-2)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 100 ℃; for 12h;

DOI:10.1002/hlca.19950780305

upstream raw materials:

DL-N-Trifluoroacetyl-α-methylvalin

2-amino-2,3-dimethylbutyramide

(2R,5S)-1-benzoyl-2-(tert-butyl)-5-isopropyl-3,5-dimethylimidazolidin-4-one

(2R,5S)-1-Benzoyl-2-(tert-butyl)-5-isopropyl-3-methylimidazolidin-4-on

Downstream raw materials:

(R)-N²-<(9H-fluoren-9-yl)methoxycarbonyl>-2-methylvaline

(S)-(+)-2-benzyloxycarbonylamino-2,3-dimethylbutanoic acid

Z-D-(αMe)Val-OH

C₉H₁₃N₂O₂^(1-)*Na⁽¹⁺⁾

Refernces

• 1、 Branca, Mathieu,Pena, Sebastien,Guillot, Regis,Gori, Didier,Alezra, Valerie,Kouklovsky, Cyrille. "Memory of chirality of tertiary aromatic amides: A simple and efficient method for the enantioselective synthesis of quaternary α-amino acids". scheme or table. p. 10711 - 10718. Retrieved 2009/12/04.
• 2、 Levine, Mindy,Kenesky, Craig Scott,Mazori, Daniel,Breslow, Ronald. "Enantioselective synthesis and enantiomeric amplification of amino acids under prebiotic conditions". supporting information; experimental part. p. 2433 - 2436. Retrieved 2009/05/27.